SN2′ reaction of organozinc reagents activated by catalytic tBu-P4 base in the presence of LiCl

Koji Kobayashi, Masahiro Ueno, Hiroshi Naka, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The tBu-P4 base was found to be an excellent catalyst for the activation of organozinc reagents. The base was used to promote the SN2′ reaction of α,β-unsaturated esters bearing a γ-chloride in the reactions with various organozinc reagents in the presence of LiCl. The reactions proceeded in high yield with excellent chemo-and regioselectivity. The role of LiCl appears to be the activation of the y-chloride of the α,β-unsaturated esters, which was confirmed by NMR spectroscopic study.

Original languageEnglish
Pages (from-to)9805-9809
Number of pages5
JournalChemistry - A European Journal
Volume15
Issue number38
DOIs
Publication statusPublished - 2009 Sep 28

Keywords

  • Lithium
  • Nucleophilic substitution
  • Phosphazene bases
  • Zinc

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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